100 Would You Rather Questions for the Holidays

The holidays — and their inevitable parties — usher in a season of group celebrations. If you want to spice up the conversations at your next gathering, try a few of these would-you-rather questions for any type of holiday event.

Family Gatherings

Would you rather have to eat a whole turkey in one sitting or never be able to eat turkey again?

Would you rather get the best gift you ever received again or get a new gift (but have no idea if it will be good or bad)?

Would you rather relive a past winter holiday again or get to travel to a future winter holiday?

Would you rather spend the holidays with your family or with three celebrities (you can choose the celebrities)?

Would you rather have to cook the big holiday meal every year or have to clean up and do the dishes after the holiday meal every year?

Would you rather be a kid or a grandparent during the holidays?

Would you rather give up one family tradition or start a new one?

Would you rather have the (skill) of (family member) or the (another skill) of (another family member)?

Would you rather get to invent a holiday on whatever day you want or have a holiday fall on your birthday?

Would you rather eat Thanksgiving food every day or never again?

Company Parties

Would you rather work only on holidays (they are still holidays) or only get holidays off work?

Would you rather switch careers entirely or stay in your career field forever?

Would you rather wear a Santa outfit or an elf outfit to work every day for a month?

Would you rather be famous for starring in a cheesy holiday movie or not be famous at all?

Would you rather have an eggnog machine instead of a coffee machine at work year-round or have your corporate dress code require ugly Christmas sweaters?

Would you rather work untangling Christmas lights or work as a mall Santa?

Would you rather have “Dreidel, Dreidel, Dreidel” stuck in your head or “Jingle Bells?”

Would you rather get amazing presents for four nights of Hanukkah and bad presents for the other four nights, or get eight OK presents?

Would you rather your office always smelled like gravy or always smelled like turkey?

Would you rather have your ears turn into elf ears or have a Santa beard forever?

This is such a great tool! Evite is well-known and great, but if you need to coordinate responses as well as volunteers and potluck items... this is the thing!!! What an awesome service you are providing. I’m in the process of planning a potentially large open-house party to celebrate life with a very sick friend in our neighborhood.... Evite could in no way handle what I needed. I’m so grateful to find your service. After only a couple hours of the sign up going live, I was already so relieved I used it!